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Pyrene derivative and organic electroluminescent element using the same

A technology of pyrene derivatives and light-emitting layers, which is applied in the field of organic electroluminescent elements, can solve the problems of insufficient luminous efficiency and lifespan of pyrene derivatives, and achieve high luminous efficiency

Inactive Publication Date: 2012-05-23
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the pyrene derivatives disclosed in Patent Document 1 to Patent Document 3 have insufficient luminous efficiency and lifetime.

Method used

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  • Pyrene derivative and organic electroluminescent element using the same
  • Pyrene derivative and organic electroluminescent element using the same
  • Pyrene derivative and organic electroluminescent element using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] Compound D-1 was synthesized according to the following scheme.

[0166] [chemical 14]

[0167]

[0168] [Synthesis of Intermediate a (Synthetic Route A)]

[0169] Under argon flow, 15.0 g (41.6 mmol) of 1,6-dibromopyrene, 25.8 g (108 mmol) of 9,9-dimethylfluoren-2-ylboronic acid, and tetrakis(tri 1.9 g (1.67 mmol) of phenylphosphine) palladium (0) [Pd (PPh3) 4 ], 27.8 g (262 mmol) of sodium carbonate (130 mL of tap water), toluene, and tetrahydrofuran were reacted at 90°C for 7 hours. After cooling, the reaction solution was filtered, and the obtained solid was washed with methanol and tap water, purified by silica gel chromatography (hot toluene), and concentrated. The obtained crude product was recrystallized from toluene and dried under reduced pressure to obtain 24.0 g of a white solid.

[0170] As a result of FD-MS (field desorption mass spectrometry) analysis on the obtained white solid, it was identified as intermediate a.

[0171] [Synthesis of Intermedi...

Embodiment 2

[0181] Compound D-2 was synthesized according to the following scheme.

[0182] [chemical 15]

[0183]

[0184] [Synthesis of Compound D-2]

[0185] Using 1-bromo-4-(trimethylsilyl)benzene instead of 1,6-dibromopyrene, using intermediate c instead of 9-dimethylfluoren-2-ylboronic acid, and intermediate a The synthesis of was reacted similarly, and the compound D-2 was synthesized.

[0186] Compound D-2 was identified by FD-MS analysis.

Embodiment 3

[0188] Compound D-3 was synthesized according to the following scheme.

[0189] [chemical 16]

[0190]

[0191] [Synthesis of Compound D-3]

[0192] Except for using 3-bromobiphenyl instead of 1,6-dibromopyrene, and using intermediate c instead of 9,9-dimethylfluoren-2-ylboronic acid, the reaction was carried out in the same manner as the synthesis of intermediate a to synthesize Compound D-3.

[0193] Compound D-3 was identified by FD-MS analysis.

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PUM

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Abstract

Provided is a pyrene derivative represented by formula (1) where, unless otherwise specified, Ar1, Ar2, and Ar3 are each independently an optionally substituted aryl group.

Description

technical field [0001] The present invention relates to a pyrene derivative and an organic electroluminescent device using the same. More specifically, it relates to a pyrene derivative capable of producing a high luminous efficiency and long-life organic electroluminescent device. Background technique [0002] The organic electroluminescence (EL) element is a self-luminous element utilizing the principle that, by applying an electric field, recombination of holes injected from an anode and electrons injected from a cathode can cause a fluorescent substance to emit light. Such an organic EL element includes a pair of electrodes including an anode and a cathode, and an organic light-emitting medium positioned between the electrodes. [0003] The organic light-emitting medium is composed of a laminate of layers having various functions, for example, a laminate in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport laye...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/66C07C255/50C07C255/51C07F7/08C09K11/06H01L51/50
CPCC09K2211/1011H05B33/10H01L51/5012C07C2103/50C07C25/22C07C255/50C07F7/0818C07C255/51C07C15/38C07C13/567C09K2211/1007C09K11/06H01L51/0054C07C2101/14C07F7/0809C07C2103/18C07C2601/14C07C2603/18C07C2603/50C07F7/0805C07F7/081H10K85/622H10K50/11C07C13/66C07F7/08
Inventor 水木由美子河村昌宏河村祐一郎齐藤博之
Owner IDEMITSU KOSAN CO LTD